NO329413B1 - Xantin-derivater, fremstilling av slike, legemidler inneholdende disse samt anvendelse derav for fremstilling av medikamenter for behandling av sykdom - Google Patents

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Publication number

NO329413B1

NO329413B1 NO20033726A NO20033726A NO329413B1 NO 329413 B1 NO329413 B1 NO 329413B1 NO 20033726 A NO20033726 A NO 20033726A NO 20033726 A NO20033726 A NO 20033726A NO 329413 B1 NO329413 B1 NO 329413B1

Authority

NO

Norway

Prior art keywords

group

amino

alkyl

methyl

substituted

Prior art date

2001-02-24

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• 238000002360 preparation method Methods 0.000 title claims description 12
• 239000003814 drug Substances 0.000 title claims description 6
• 238000004519 manufacturing process Methods 0.000 title claims description 5
• 201000010099 disease Diseases 0.000 title description 5
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title description 5
• -1 difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, phenoxy, benzyloxy - Chemical class 0.000 claims description 1270
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 132
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 128
• 150000001875 compounds Chemical class 0.000 claims description 117
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 97
• 125000003277 amino group Chemical group 0.000 claims description 94
• 125000000217 alkyl group Chemical group 0.000 claims description 92
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 91
• 229910052731 fluorine Inorganic materials 0.000 claims description 72
• 125000004432 carbon atom Chemical group C* 0.000 claims description 67
• 229910052801 chlorine Inorganic materials 0.000 claims description 67
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 65
• 239000011737 fluorine Substances 0.000 claims description 64
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 63
• 239000000460 chlorine Substances 0.000 claims description 63
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 61
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 61
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 59
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 58
• 229940075420 xanthine Drugs 0.000 claims description 58
• 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims description 52
• 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 49
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 48
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 42
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 42
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 38
• 125000003342 alkenyl group Chemical group 0.000 claims description 35
• 150000003839 salts Chemical class 0.000 claims description 31
• 239000000203 mixture Substances 0.000 claims description 28
• 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 27
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 27
• LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 claims description 25
• 229910052740 iodine Inorganic materials 0.000 claims description 24
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 24
• 238000006243 chemical reaction Methods 0.000 claims description 22
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 20
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 18
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 17
• 125000001072 heteroaryl group Chemical group 0.000 claims description 17
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 15
• 125000001153 fluoro group Chemical group F* 0.000 claims description 15
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 14
• XJNKUWDMCBZMTG-UHFFFAOYSA-N 2-[[8-(3-aminopiperidin-1-yl)-1,3-dimethyl-2,6-dioxopurin-7-yl]methyl]benzonitrile Chemical compound C=1C=CC=C(C#N)C=1CN1C=2C(=O)N(C)C(=O)N(C)C=2N=C1N1CCCC(N)C1 XJNKUWDMCBZMTG-UHFFFAOYSA-N 0.000 claims description 14
• IZFULWYJEKPZFC-UHFFFAOYSA-N 8-(3-aminoazepan-1-yl)-7-benzyl-1,3-dimethylpurine-2,6-dione Chemical compound C=1C=CC=CC=1CN1C=2C(=O)N(C)C(=O)N(C)C=2N=C1N1CCCCC(N)C1 IZFULWYJEKPZFC-UHFFFAOYSA-N 0.000 claims description 14
• SQOXLWWIJJBBID-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-[(2-iodophenyl)methyl]-1,3-dimethylpurine-2,6-dione Chemical compound C=1C=CC=C(I)C=1CN1C=2C(=O)N(C)C(=O)N(C)C=2N=C1N1CCCC(N)C1 SQOXLWWIJJBBID-UHFFFAOYSA-N 0.000 claims description 14
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 14
• 229910052799 carbon Inorganic materials 0.000 claims description 14
• 125000000623 heterocyclic group Chemical group 0.000 claims description 14
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 14
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 14
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
• 229910052739 hydrogen Inorganic materials 0.000 claims description 13
• 239000001257 hydrogen Substances 0.000 claims description 13
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
• 125000003545 alkoxy group Chemical group 0.000 claims description 12
• 125000003118 aryl group Chemical group 0.000 claims description 12
• 125000004429 atom Chemical group 0.000 claims description 12
• 229910052794 bromium Inorganic materials 0.000 claims description 12
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 12
• 239000000126 substance Substances 0.000 claims description 12
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 11
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 11
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 11
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
• 229910052757 nitrogen Inorganic materials 0.000 claims description 11
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
• 125000001624 naphthyl group Chemical group 0.000 claims description 10
• 125000004076 pyridyl group Chemical group 0.000 claims description 10
• 125000001544 thienyl group Chemical group 0.000 claims description 10
• 125000003282 alkyl amino group Chemical group 0.000 claims description 9
• 125000000304 alkynyl group Chemical group 0.000 claims description 9
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 9
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 8
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 8
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 8
• 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
• 150000001721 carbon Chemical group 0.000 claims description 8
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 8
• 125000002541 furyl group Chemical group 0.000 claims description 8
• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 8
• 125000004998 naphthylethyl group Chemical group C1(=CC=CC2=CC=CC=C12)CC* 0.000 claims description 8
• 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 claims description 8
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 8
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 7
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 7
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 7
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
• 238000000034 method Methods 0.000 claims description 7
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 7
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
• FKKUHLHWSINVFV-UHFFFAOYSA-N 2-[[8-(3-aminopyrrolidin-1-yl)-1,3-dimethyl-2,6-dioxopurin-7-yl]methyl]benzonitrile Chemical compound C=1C=CC=C(C#N)C=1CN1C=2C(=O)N(C)C(=O)N(C)C=2N=C1N1CCC(N)C1 FKKUHLHWSINVFV-UHFFFAOYSA-N 0.000 claims description 6
• HQAPWGWQFPRNLO-UHFFFAOYSA-N 8-(3-aminopyrrolidin-1-yl)-7-[(2-bromophenyl)methyl]-1,3-dimethylpurine-2,6-dione Chemical compound C=1C=CC=C(Br)C=1CN1C=2C(=O)N(C)C(=O)N(C)C=2N=C1N1CCC(N)C1 HQAPWGWQFPRNLO-UHFFFAOYSA-N 0.000 claims description 6
• BWWNGDCYAMCKFX-UHFFFAOYSA-N 8-(3-aminopyrrolidin-1-yl)-7-[(2-iodophenyl)methyl]-1,3-dimethylpurine-2,6-dione Chemical compound C=1C=CC=C(I)C=1CN1C=2C(=O)N(C)C(=O)N(C)C=2N=C1N1CCC(N)C1 BWWNGDCYAMCKFX-UHFFFAOYSA-N 0.000 claims description 6
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 6
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 6
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 6
• 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 6
• 230000009467 reduction Effects 0.000 claims description 6
• 238000006722 reduction reaction Methods 0.000 claims description 6
• 125000001424 substituent group Chemical group 0.000 claims description 6
• 125000006173 tetrahydropyranylmethyl group Chemical group 0.000 claims description 6
• 125000000335 thiazolyl group Chemical group 0.000 claims description 6
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
• 125000002252 acyl group Chemical group 0.000 claims description 5
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 5
• 150000001412 amines Chemical class 0.000 claims description 5
• 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 5
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 5
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 5
• 125000006223 tetrahydrofuranylmethyl group Chemical group 0.000 claims description 5
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
• 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 claims description 4
• 150000001408 amides Chemical class 0.000 claims description 4
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
• 206010012601 diabetes mellitus Diseases 0.000 claims description 4
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 4
• 150000002148 esters Chemical class 0.000 claims description 4
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
• 125000001041 indolyl group Chemical group 0.000 claims description 4
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 4
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
• 229940126601 medicinal product Drugs 0.000 claims description 4
• 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 4
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
• 125000002971 oxazolyl group Chemical group 0.000 claims description 4
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• 239000001301 oxygen Substances 0.000 claims description 4
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 4
• 229910052717 sulfur Inorganic materials 0.000 claims description 4
• 125000004434 sulfur atom Chemical group 0.000 claims description 4
• 125000005302 thiazolylmethyl group Chemical group [H]C1=C([H])N=C(S1)C([H])([H])* 0.000 claims description 4
• 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims description 4
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 3
• KBRMUYSIOXYFQA-UHFFFAOYSA-N 1,3-dimethyl-8-[3-(methylamino)piperidin-1-yl]-7-(3-methylbut-2-enyl)purine-2,6-dione Chemical compound C1C(NC)CCCN1C(N1CC=C(C)C)=NC2=C1C(=O)N(C)C(=O)N2C KBRMUYSIOXYFQA-UHFFFAOYSA-N 0.000 claims description 3
• 230000010933 acylation Effects 0.000 claims description 3
• 238000005917 acylation reaction Methods 0.000 claims description 3
• 230000029936 alkylation Effects 0.000 claims description 3
• 238000005804 alkylation reaction Methods 0.000 claims description 3
• 239000000969 carrier Substances 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims description 3
• 230000032050 esterification Effects 0.000 claims description 3
• 238000005886 esterification reaction Methods 0.000 claims description 3
• 150000007522 mineralic acids Chemical class 0.000 claims description 3
• 230000009935 nitrosation Effects 0.000 claims description 3
• 238000007034 nitrosation reaction Methods 0.000 claims description 3
• 150000007524 organic acids Chemical class 0.000 claims description 3
• 235000005985 organic acids Nutrition 0.000 claims description 3
• 125000006239 protecting group Chemical group 0.000 claims description 3
• 238000005932 reductive alkylation reaction Methods 0.000 claims description 3
• 125000006602 (C1-C3) alkylsulfonylamino group Chemical group 0.000 claims description 2
• BAFXHIFZTPPZRV-UHFFFAOYSA-N 8-(3-aminoazepan-1-yl)-1,3-dimethyl-7-(3-methylbut-2-enyl)purine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(C)C(=O)C=2N(CC=C(C)C)C=1N1CCCCC(N)C1 BAFXHIFZTPPZRV-UHFFFAOYSA-N 0.000 claims description 2
• IAKWAVSFCREPJB-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-1,3-dimethyl-7-(thiophen-2-ylmethyl)purine-2,6-dione Chemical compound C=1C=CSC=1CN1C=2C(=O)N(C)C(=O)N(C)C=2N=C1N1CCCC(N)C1 IAKWAVSFCREPJB-UHFFFAOYSA-N 0.000 claims description 2
• IUCRVQNYRNKWOY-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-1-[2-(2-methoxyphenyl)-2-oxoethyl]-3-methyl-7-(3-methylbut-2-enyl)purine-2,6-dione Chemical compound COC1=CC=CC=C1C(=O)CN1C(=O)C(N(CC=C(C)C)C(N2CC(N)CCC2)=N2)=C2N(C)C1=O IUCRVQNYRNKWOY-UHFFFAOYSA-N 0.000 claims description 2
• QCPGHHSDDWAKKQ-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-3-methyl-7-(3-methylbut-2-enyl)-1-(2-oxo-2-thiophen-3-ylethyl)purine-2,6-dione Chemical compound O=C1C=2N(CC=C(C)C)C(N3CC(N)CCC3)=NC=2N(C)C(=O)N1CC(=O)C=1C=CSC=1 QCPGHHSDDWAKKQ-UHFFFAOYSA-N 0.000 claims description 2
• SNYHIIMDELHQNH-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-3-methyl-7-(3-methylbut-2-enyl)-1-(2-thiophen-2-ylethyl)purine-2,6-dione Chemical compound O=C1C=2N(CC=C(C)C)C(N3CC(N)CCC3)=NC=2N(C)C(=O)N1CCC1=CC=CS1 SNYHIIMDELHQNH-UHFFFAOYSA-N 0.000 claims description 2
• ZJQIERZOSFTHMF-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-3-methyl-7-(3-methylbut-2-enyl)-1-(2-thiophen-3-ylethyl)purine-2,6-dione Chemical compound O=C1C=2N(CC=C(C)C)C(N3CC(N)CCC3)=NC=2N(C)C(=O)N1CCC=1C=CSC=1 ZJQIERZOSFTHMF-UHFFFAOYSA-N 0.000 claims description 2
• FBDRYCWNKRSQKM-NTCAYCPXSA-N 8-(3-aminopiperidin-1-yl)-3-methyl-7-(3-methylbut-2-enyl)-1-[(e)-2-phenylethenyl]purine-2,6-dione Chemical compound O=C1C=2N(CC=C(C)C)C(N3CC(N)CCC3)=NC=2N(C)C(=O)N1\C=C\C1=CC=CC=C1 FBDRYCWNKRSQKM-NTCAYCPXSA-N 0.000 claims description 2
• CNEWMJQRVPTIHS-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-3-methyl-7-(3-methylbut-2-enyl)-1-[2-(2-methylphenyl)ethyl]purine-2,6-dione Chemical compound O=C1C=2N(CC=C(C)C)C(N3CC(N)CCC3)=NC=2N(C)C(=O)N1CCC1=CC=CC=C1C CNEWMJQRVPTIHS-UHFFFAOYSA-N 0.000 claims description 2
• ODYKCZITKULMQD-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-3-methyl-7-(3-methylbut-2-enyl)-1-[2-(3-methylphenyl)ethyl]purine-2,6-dione Chemical compound O=C1C=2N(CC=C(C)C)C(N3CC(N)CCC3)=NC=2N(C)C(=O)N1CCC1=CC=CC(C)=C1 ODYKCZITKULMQD-UHFFFAOYSA-N 0.000 claims description 2
• VYJQZDKKKPTAPR-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-[(2-fluorophenyl)methyl]-1,3-dimethylpurine-2,6-dione Chemical compound C=1C=CC=C(F)C=1CN1C=2C(=O)N(C)C(=O)N(C)C=2N=C1N1CCCC(N)C1 VYJQZDKKKPTAPR-UHFFFAOYSA-N 0.000 claims description 2
• ZOAKVRKCPUVXOG-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-[(3-fluorophenyl)methyl]-1,3-dimethylpurine-2,6-dione Chemical compound C=1C=CC(F)=CC=1CN1C=2C(=O)N(C)C(=O)N(C)C=2N=C1N1CCCC(N)C1 ZOAKVRKCPUVXOG-UHFFFAOYSA-N 0.000 claims description 2
• IKKFCXGLVARIQR-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-[(4-fluorophenyl)methyl]-1,3-dimethylpurine-2,6-dione Chemical compound C=1C=C(F)C=CC=1CN1C=2C(=O)N(C)C(=O)N(C)C=2N=C1N1CCCC(N)C1 IKKFCXGLVARIQR-UHFFFAOYSA-N 0.000 claims description 2
• KSWQSBBOSLLRAR-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-benzyl-1,3-bis(cyclopropylmethyl)purine-2,6-dione Chemical compound C1C(N)CCCN1C(N1CC=2C=CC=CC=2)=NC2=C1C(=O)N(CC1CC1)C(=O)N2CC1CC1 KSWQSBBOSLLRAR-UHFFFAOYSA-N 0.000 claims description 2
• FODNGCIHDALBIQ-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-but-2-enyl-1,3-dimethylpurine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(C)C(=O)C=2N(CC=CC)C=1N1CCCC(N)C1 FODNGCIHDALBIQ-UHFFFAOYSA-N 0.000 claims description 2
• TZUVZEOIPZGZAT-UHFFFAOYSA-N 8-(4-aminoazepan-1-yl)-1,3-dimethyl-7-(3-methylbut-2-enyl)purine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(C)C(=O)C=2N(CC=C(C)C)C=1N1CCCC(N)CC1 TZUVZEOIPZGZAT-UHFFFAOYSA-N 0.000 claims description 2
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• DOCBNOXEORTAPR-UHFFFAOYSA-N methyl 2-(7-benzyl-1-methyl-2,6-dioxopurin-3-yl)acetate Chemical compound C1=2C(=O)N(C)C(=O)N(CC(=O)OC)C=2N=CN1CC1=CC=CC=C1 DOCBNOXEORTAPR-UHFFFAOYSA-N 0.000 description 1
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• DYGXOELWUBFQKL-UHFFFAOYSA-N methyl 2-[2-[2-[3-methyl-7-(3-methylbut-2-enyl)-8-[3-[(2-methylpropan-2-yl)oxycarbonylamino]piperidin-1-yl]-2,6-dioxopurin-1-yl]acetyl]phenoxy]acetate Chemical compound COC(=O)COC1=CC=CC=C1C(=O)CN1C(=O)C(N(CC=C(C)C)C(N2CC(CCC2)NC(=O)OC(C)(C)C)=N2)=C2N(C)C1=O DYGXOELWUBFQKL-UHFFFAOYSA-N 0.000 description 1
• WKMNDKURUUJQCO-UHFFFAOYSA-N methyl 2-[3-[2-[3-methyl-7-(3-methylbut-2-enyl)-8-[3-[(2-methylpropan-2-yl)oxycarbonylamino]piperidin-1-yl]-2,6-dioxopurin-1-yl]acetyl]phenoxy]acetate Chemical compound COC(=O)COC1=CC=CC(C(=O)CN2C(C=3N(CC=C(C)C)C(N4CC(CCC4)NC(=O)OC(C)(C)C)=NC=3N(C)C2=O)=O)=C1 WKMNDKURUUJQCO-UHFFFAOYSA-N 0.000 description 1
• SPUJNDSUMKOLDX-INIZCTEOSA-N methyl 2-[3-methyl-7-(3-methylbut-2-enyl)-8-[(3s)-3-[(2-methylpropan-2-yl)oxycarbonylamino]piperidin-1-yl]-2,6-dioxopurin-1-yl]acetate Chemical compound CC(C)=CCN1C=2C(=O)N(CC(=O)OC)C(=O)N(C)C=2N=C1N1CCC[C@H](NC(=O)OC(C)(C)C)C1 SPUJNDSUMKOLDX-INIZCTEOSA-N 0.000 description 1
• SBXWQNYODBCYSI-UHFFFAOYSA-N methyl 2-[7-(3-methylbut-2-enyl)-8-[3-[(2-methylpropan-2-yl)oxycarbonylamino]piperidin-1-yl]-2,6-dioxo-1-(2-phenylethyl)purin-3-yl]acetate Chemical compound CC(C)=CCN1C=2C(=O)N(CCC=3C=CC=CC=3)C(=O)N(CC(=O)OC)C=2N=C1N1CCCC(NC(=O)OC(C)(C)C)C1 SBXWQNYODBCYSI-UHFFFAOYSA-N 0.000 description 1
• WIUUQQMQCMYJDZ-UHFFFAOYSA-N methyl 2-[7-(3-methylbut-2-enyl)-8-[3-[(2-methylpropan-2-yl)oxycarbonylamino]piperidin-1-yl]-2,6-dioxopurin-3-yl]acetate Chemical compound CC(C)=CCN1C=2C(=O)NC(=O)N(CC(=O)OC)C=2N=C1N1CCCC(NC(=O)OC(C)(C)C)C1 WIUUQQMQCMYJDZ-UHFFFAOYSA-N 0.000 description 1
• CVEBBPWJKZUFSG-UHFFFAOYSA-N methyl 2-[[3-methyl-7-(3-methylbut-2-enyl)-8-[3-[(2-methylpropan-2-yl)oxycarbonylamino]piperidin-1-yl]-2,6-dioxopurin-1-yl]methyl]prop-2-enoate Chemical compound CC(C)=CCN1C=2C(=O)N(CC(=C)C(=O)OC)C(=O)N(C)C=2N=C1N1CCCC(NC(=O)OC(C)(C)C)C1 CVEBBPWJKZUFSG-UHFFFAOYSA-N 0.000 description 1
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• LSYLLMYSTICUBX-SFHVURJKSA-N methyl 4-[3-methyl-7-(3-methylbut-2-enyl)-8-[(3s)-3-[(2-methylpropan-2-yl)oxycarbonylamino]piperidin-1-yl]-2,6-dioxopurin-1-yl]butanoate Chemical compound CC(C)=CCN1C=2C(=O)N(CCCC(=O)OC)C(=O)N(C)C=2N=C1N1CCC[C@H](NC(=O)OC(C)(C)C)C1 LSYLLMYSTICUBX-SFHVURJKSA-N 0.000 description 1
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• BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
• 239000012312 sodium hydride Substances 0.000 description 1
• 229910000104 sodium hydride Inorganic materials 0.000 description 1
• 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
• 239000000600 sorbitol Substances 0.000 description 1
• 125000000547 substituted alkyl group Chemical group 0.000 description 1
• 239000000758 substrate Substances 0.000 description 1
• 229960004793 sucrose Drugs 0.000 description 1
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• 239000000829 suppository Substances 0.000 description 1
• 239000000725 suspension Substances 0.000 description 1
• 229940065721 systemic for obstructive airway disease xanthines Drugs 0.000 description 1
• 239000003826 tablet Substances 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• FMMFFOJDQZOCHS-UHFFFAOYSA-N tert-butyl 3-(1,3-dimethyl-2,6-dioxo-7h-purin-8-yl)piperidine-1-carboxylate Chemical compound N1C=2C(=O)N(C)C(=O)N(C)C=2N=C1C1CCCN(C(=O)OC(C)(C)C)C1 FMMFFOJDQZOCHS-UHFFFAOYSA-N 0.000 description 1
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• GBRZXURGNWSHOT-UHFFFAOYSA-N tert-butyl n-(1-benzylazepan-4-yl)carbamate Chemical compound C1CC(NC(=O)OC(C)(C)C)CCCN1CC1=CC=CC=C1 GBRZXURGNWSHOT-UHFFFAOYSA-N 0.000 description 1
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• QEVWCEYVNCWPKJ-RNFRBKRXSA-N tert-butyl n-[(1r,2r)-2-aminocyclobutyl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H]1CC[C@H]1N QEVWCEYVNCWPKJ-RNFRBKRXSA-N 0.000 description 1
• HZFJIGLHVCOVAK-JKSUJKDBSA-N tert-butyl n-[(1r,3s)-3-[1,3-dimethyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]cyclohexyl]carbamate Chemical compound N=1C=2N(C)C(=O)N(C)C(=O)C=2N(CC=C(C)C)C=1[C@H]1CCC[C@@H](NC(=O)OC(C)(C)C)C1 HZFJIGLHVCOVAK-JKSUJKDBSA-N 0.000 description 1
• IALCKOUAFJPAMT-CABCVRRESA-N tert-butyl n-[(1s,2r)-2-[[1,3-dimethyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]amino]cyclopentyl]carbamate Chemical compound N=1C=2N(C)C(=O)N(C)C(=O)C=2N(CC=C(C)C)C=1N[C@@H]1CCC[C@@H]1NC(=O)OC(C)(C)C IALCKOUAFJPAMT-CABCVRRESA-N 0.000 description 1
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• ATTCQYNOZGXUII-JOCHJYFZSA-N tert-butyl n-[(3r)-1-[3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxo-1-(2-phenylethyl)purin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC=C(C)C)C(N3C[C@@H](CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CCC1=CC=CC=C1 ATTCQYNOZGXUII-JOCHJYFZSA-N 0.000 description 1
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• TUJAXGOQSUAROV-CQSZACIVSA-N tert-butyl n-[(3r)-1-[3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)NC(=O)C=2N(CC=C(C)C)C=1N1CCC[C@@H](NC(=O)OC(C)(C)C)C1 TUJAXGOQSUAROV-CQSZACIVSA-N 0.000 description 1
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• AATHUGYAFTVFLA-QFIPXVFZSA-N tert-butyl n-[(3s)-1-(7-benzyl-3-hexyl-1-methyl-2,6-dioxopurin-8-yl)piperidin-3-yl]carbamate Chemical compound C=1C=CC=CC=1CN1C=2C(=O)N(C)C(=O)N(CCCCCC)C=2N=C1N1CCC[C@H](NC(=O)OC(C)(C)C)C1 AATHUGYAFTVFLA-QFIPXVFZSA-N 0.000 description 1
• RKCVJJDVMGDHQE-HNNXBMFYSA-N tert-butyl n-[(3s)-1-[1,3-dimethyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(C)C(=O)C=2N(CC=C(C)C)C=1N1CCC[C@H](NC(=O)OC(C)(C)C)C1 RKCVJJDVMGDHQE-HNNXBMFYSA-N 0.000 description 1
• IPUAFUXZHPMMQV-QFIPXVFZSA-N tert-butyl n-[(3s)-1-[1-(isoquinolin-1-ylmethyl)-3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4C=CN=3)C(=O)C=2N(CC=C(C)C)C=1N1CCC[C@H](NC(=O)OC(C)(C)C)C1 IPUAFUXZHPMMQV-QFIPXVFZSA-N 0.000 description 1
• TUCSIQRTIYSWEF-SANMLTNESA-N tert-butyl n-[(3s)-1-[1-[2-[3-[tert-butyl(dimethyl)silyl]oxyphenyl]ethyl]-3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC=C(C)C)C(N3C[C@H](CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CCC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1 TUCSIQRTIYSWEF-SANMLTNESA-N 0.000 description 1
• CBMSZYWITHQUSQ-SANMLTNESA-N tert-butyl n-[(3s)-1-[1-[2-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]ethyl]-3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC=C(C)C)C(N3C[C@H](CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1 CBMSZYWITHQUSQ-SANMLTNESA-N 0.000 description 1
• ATTCQYNOZGXUII-QFIPXVFZSA-N tert-butyl n-[(3s)-1-[3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxo-1-(2-phenylethyl)purin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC=C(C)C)C(N3C[C@H](CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CCC1=CC=CC=C1 ATTCQYNOZGXUII-QFIPXVFZSA-N 0.000 description 1
• TUJAXGOQSUAROV-AWEZNQCLSA-N tert-butyl n-[(3s)-1-[3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)NC(=O)C=2N(CC=C(C)C)C=1N1CCC[C@H](NC(=O)OC(C)(C)C)C1 TUJAXGOQSUAROV-AWEZNQCLSA-N 0.000 description 1
• YNUINTOEOQDOGY-SFHVURJKSA-N tert-butyl n-[(3s)-1-[7-benzyl-3-(2-hydroxyethyl)-1-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound C=1C=CC=CC=1CN1C=2C(=O)N(C)C(=O)N(CCO)C=2N=C1N1CCC[C@H](NC(=O)OC(C)(C)C)C1 YNUINTOEOQDOGY-SFHVURJKSA-N 0.000 description 1
• SOQWOKFJKAEWRW-QHCPKHFHSA-N tert-butyl n-[(3s)-1-[7-benzyl-3-[(4-methoxyphenyl)methyl]-1-methyl-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N(C)C(=O)C(N2CC=3C=CC=CC=3)=C1N=C2N1C[C@@H](NC(=O)OC(C)(C)C)CCC1 SOQWOKFJKAEWRW-QHCPKHFHSA-N 0.000 description 1
• WUOQXNWMYLFAHT-QMMMGPOBSA-N tert-butyl n-[(3s)-piperidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@H]1CCCNC1 WUOQXNWMYLFAHT-QMMMGPOBSA-N 0.000 description 1
• VKWASISDMCRNCV-UHFFFAOYSA-N tert-butyl n-[1,3-bis(methylamino)-1-oxopropan-2-yl]carbamate Chemical compound CNCC(C(=O)NC)NC(=O)OC(C)(C)C VKWASISDMCRNCV-UHFFFAOYSA-N 0.000 description 1
• VDTVZPMQOCGQOY-UHFFFAOYSA-N tert-butyl n-[1-(dimethylamino)-3-[[1,3-dimethyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]-methylamino]-1-oxopropan-2-yl]carbamate Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=C(N(C)CC(C(=O)N(C)C)NC(=O)OC(C)(C)C)N2CC=C(C)C VDTVZPMQOCGQOY-UHFFFAOYSA-N 0.000 description 1
• OSEYPIAGCKLDCH-UHFFFAOYSA-N tert-butyl n-[1-[1,3-dimethyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]-1,4-diazepan-6-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(C)C(=O)C=2N(CC=C(C)C)C=1N1CCNCC(NC(=O)OC(C)(C)C)C1 OSEYPIAGCKLDCH-UHFFFAOYSA-N 0.000 description 1
• WCCWFXWDZZKZOI-UHFFFAOYSA-N tert-butyl n-[1-[1,3-dimethyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]-3-methylpiperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(C)C(=O)C=2N(CC=C(C)C)C=1N1CCCC(C)(NC(=O)OC(C)(C)C)C1 WCCWFXWDZZKZOI-UHFFFAOYSA-N 0.000 description 1
• HLNQKDBHLSDDQK-UHFFFAOYSA-N tert-butyl n-[1-[1,3-dimethyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]-4-methylpiperidin-3-yl]carbamate Chemical compound C1C(NC(=O)OC(C)(C)C)C(C)CCN1C(N1CC=C(C)C)=NC2=C1C(=O)N(C)C(=O)N2C HLNQKDBHLSDDQK-UHFFFAOYSA-N 0.000 description 1
• OZFZZENFEYSQGM-UHFFFAOYSA-N tert-butyl n-[1-[1,3-dimethyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]azepan-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(C)C(=O)C=2N(CC=C(C)C)C=1N1CCCCC(NC(=O)OC(C)(C)C)C1 OZFZZENFEYSQGM-UHFFFAOYSA-N 0.000 description 1
• CENVGJSMXPIMFK-UHFFFAOYSA-N tert-butyl n-[1-[1,3-dimethyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]azepan-4-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(C)C(=O)C=2N(CC=C(C)C)C=1N1CCCC(NC(=O)OC(C)(C)C)CC1 CENVGJSMXPIMFK-UHFFFAOYSA-N 0.000 description 1
• HNCHNVAUMOAWDS-UHFFFAOYSA-N tert-butyl n-[1-[1-(isoquinolin-4-ylmethyl)-3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4C=NC=3)C(=O)C=2N(CC=C(C)C)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 HNCHNVAUMOAWDS-UHFFFAOYSA-N 0.000 description 1
• WFOUXHIOVMYZTP-UHFFFAOYSA-N tert-butyl n-[1-[1-[(5-aminoisoquinolin-1-yl)methyl]-3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC(N)=C4C=CN=3)C(=O)C=2N(CC=C(C)C)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 WFOUXHIOVMYZTP-UHFFFAOYSA-N 0.000 description 1
• SUPMVGKPNMRPGN-UHFFFAOYSA-N tert-butyl n-[1-[1-[2-(2,5-dimethoxyphenyl)-2-oxoethyl]-3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound COC1=CC=C(OC)C(C(=O)CN2C(C=3N(CC=C(C)C)C(N4CC(CCC4)NC(=O)OC(C)(C)C)=NC=3N(C)C2=O)=O)=C1 SUPMVGKPNMRPGN-UHFFFAOYSA-N 0.000 description 1
• YDJDBKTWGFBOPV-UHFFFAOYSA-N tert-butyl n-[1-[1-[2-(2-hydroxyphenyl)-2-oxoethyl]-3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CC(=O)C1=CC=CC=C1O YDJDBKTWGFBOPV-UHFFFAOYSA-N 0.000 description 1
• NNCWGVNUCMJGLO-UHFFFAOYSA-N tert-butyl n-[1-[1-[2-(2-methoxyphenyl)-2-oxoethyl]-3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound COC1=CC=CC=C1C(=O)CN1C(=O)C(N(CC=C(C)C)C(N2CC(CCC2)NC(=O)OC(C)(C)C)=N2)=C2N(C)C1=O NNCWGVNUCMJGLO-UHFFFAOYSA-N 0.000 description 1
• RRJDNFOYFHJCNS-UHFFFAOYSA-N tert-butyl n-[1-[1-[2-(3,5-difluorophenyl)ethyl]-3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CCC1=CC(F)=CC(F)=C1 RRJDNFOYFHJCNS-UHFFFAOYSA-N 0.000 description 1
• UGWIRHINVMNUBX-UHFFFAOYSA-N tert-butyl n-[1-[1-[2-[2-[bis(methylsulfonyl)amino]phenyl]-2-oxoethyl]-3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CC(=O)C1=CC=CC=C1N(S(C)(=O)=O)S(C)(=O)=O UGWIRHINVMNUBX-UHFFFAOYSA-N 0.000 description 1
• WQWCYZRZOGRNMZ-UHFFFAOYSA-N tert-butyl n-[1-[1-[2-[3-(2-amino-2-oxoethoxy)phenyl]-2-oxoethyl]-3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CC(=O)C1=CC=CC(OCC(N)=O)=C1 WQWCYZRZOGRNMZ-UHFFFAOYSA-N 0.000 description 1
• VXKNVQRNDWVQDY-UHFFFAOYSA-N tert-butyl n-[1-[1-[2-[3-(ethoxycarbonylcarbamoylamino)phenyl]-2-oxoethyl]-3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound CCOC(=O)NC(=O)NC1=CC=CC(C(=O)CN2C(C=3N(CC=C(C)C)C(N4CC(CCC4)NC(=O)OC(C)(C)C)=NC=3N(C)C2=O)=O)=C1 VXKNVQRNDWVQDY-UHFFFAOYSA-N 0.000 description 1
• UFRMUBXTLXPEJG-UHFFFAOYSA-N tert-butyl n-[1-[1-[2-[3-(methanesulfonamido)phenyl]-2-oxoethyl]-3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CC(=O)C1=CC=CC(NS(C)(=O)=O)=C1 UFRMUBXTLXPEJG-UHFFFAOYSA-N 0.000 description 1
• VVTGVIHHMDEYNF-UHFFFAOYSA-N tert-butyl n-[1-[1-[2-[3-[2-(dimethylamino)-2-oxoethoxy]phenyl]-2-oxoethyl]-3-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound CN(C)C(=O)COC1=CC=CC(C(=O)CN2C(C=3N(CC=C(C)C)C(N4CC(CCC4)NC(=O)OC(C)(C)C)=NC=3N(C)C2=O)=O)=C1 VVTGVIHHMDEYNF-UHFFFAOYSA-N 0.000 description 1
• DDLRNVHEXIBFPM-UHFFFAOYSA-N tert-butyl n-[1-[1-amino-7-(3-methylbutyl)-2,6-dioxo-3h-purin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2NC(=O)N(N)C(=O)C=2N(CCC(C)C)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 DDLRNVHEXIBFPM-UHFFFAOYSA-N 0.000 description 1
• RFPJGBIGLOTTHF-UHFFFAOYSA-N tert-butyl n-[1-[1-benzamido-7-(3-methylbutyl)-2,6-dioxo-3h-purin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CCC(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2NC(=O)N1NC(=O)C1=CC=CC=C1 RFPJGBIGLOTTHF-UHFFFAOYSA-N 0.000 description 1
• OPEQUASEBUWSKN-UHFFFAOYSA-N tert-butyl n-[1-[1-methyl-7-(3-methylbut-2-enyl)-2,6-dioxo-3-(2-phenylethyl)purin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1N(C)C(=O)C=2N(CC=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N1CCC1=CC=CC=C1 OPEQUASEBUWSKN-UHFFFAOYSA-N 0.000 description 1
• FMDNFFQCPMVKJV-UHFFFAOYSA-N tert-butyl n-[1-[1-methyl-7-(3-methylbut-2-enyl)-2,6-dioxo-3-(4-phenylbutyl)purin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1N(C)C(=O)C=2N(CC=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N1CCCCC1=CC=CC=C1 FMDNFFQCPMVKJV-UHFFFAOYSA-N 0.000 description 1
• YGPJUURXTXWBGA-OBGWFSINSA-N tert-butyl n-[1-[1-methyl-7-(3-methylbut-2-enyl)-2,6-dioxo-3-[(e)-2-phenylethenyl]purin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1N(C)C(=O)C=2N(CC=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N1\C=C\C1=CC=CC=C1 YGPJUURXTXWBGA-OBGWFSINSA-N 0.000 description 1
• CAVONGYBKYIXSH-UHFFFAOYSA-N tert-butyl n-[1-[1-methyl-7-(3-methylbut-2-enyl)-2,6-dioxo-3-phenacylpurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1N(C)C(=O)C=2N(CC=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N1CC(=O)C1=CC=CC=C1 CAVONGYBKYIXSH-UHFFFAOYSA-N 0.000 description 1
• YWDQXYRBSHXYSO-UHFFFAOYSA-N tert-butyl n-[1-[1-methyl-7-(3-methylbut-2-enyl)-2,6-dioxo-3-phenylpurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1N(C)C(=O)C=2N(CC=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N1C1=CC=CC=C1 YWDQXYRBSHXYSO-UHFFFAOYSA-N 0.000 description 1
• PGBBJOGNPTVONT-UHFFFAOYSA-N tert-butyl n-[1-[1-methyl-7-(3-methylbut-2-enyl)-2,6-dioxo-3h-purin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2NC(=O)N(C)C(=O)C=2N(CC=C(C)C)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 PGBBJOGNPTVONT-UHFFFAOYSA-N 0.000 description 1
• RKUXARHWUODGDR-UHFFFAOYSA-N tert-butyl n-[1-[1-methyl-7-(3-methylbut-2-enyl)-3-[2-(3-methylphenyl)ethyl]-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1N(C)C(=O)C=2N(CC=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N1CCC1=CC=CC(C)=C1 RKUXARHWUODGDR-UHFFFAOYSA-N 0.000 description 1
• FOZGNLXHPSLWDE-UHFFFAOYSA-N tert-butyl n-[1-[1-methyl-7-(3-methylbut-2-enyl)-3-[2-(4-methylphenyl)ethyl]-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1N(C)C(=O)C=2N(CC=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N1CCC1=CC=C(C)C=C1 FOZGNLXHPSLWDE-UHFFFAOYSA-N 0.000 description 1
• FGMCPZWLVJGUIN-UHFFFAOYSA-N tert-butyl n-[1-[3-(cyanomethyl)-1-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(CC#N)C(=O)N(C)C(=O)C=2N(CC=C(C)C)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 FGMCPZWLVJGUIN-UHFFFAOYSA-N 0.000 description 1
• UZZRYGHFXLEILP-UHFFFAOYSA-N tert-butyl n-[1-[3-(cyanomethyl)-7-(3-methylbut-2-enyl)-2,6-dioxo-1-(2-phenylethyl)purin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(CC#N)C(=O)N1CCC1=CC=CC=C1 UZZRYGHFXLEILP-UHFFFAOYSA-N 0.000 description 1
• CAFGEUVZUMTEAP-UHFFFAOYSA-N tert-butyl n-[1-[3-[2-(2-fluorophenyl)ethyl]-1-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1N(C)C(=O)C=2N(CC=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N1CCC1=CC=CC=C1F CAFGEUVZUMTEAP-UHFFFAOYSA-N 0.000 description 1
• HNIYRZAINWLXJX-UHFFFAOYSA-N tert-butyl n-[1-[3-[2-(3-methoxyphenyl)ethyl]-1-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound COC1=CC=CC(CCN2C(N(C)C(=O)C=3N(CC=C(C)C)C(N4CC(CCC4)NC(=O)OC(C)(C)C)=NC=32)=O)=C1 HNIYRZAINWLXJX-UHFFFAOYSA-N 0.000 description 1
• NMIVGZVTGFHOTR-UHFFFAOYSA-N tert-butyl n-[1-[3-[2-(4-fluorophenyl)ethyl]-1-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1N(C)C(=O)C=2N(CC=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N1CCC1=CC=C(F)C=C1 NMIVGZVTGFHOTR-UHFFFAOYSA-N 0.000 description 1
• GAFHTHIEYSJDOG-UHFFFAOYSA-N tert-butyl n-[1-[3-[2-(4-methoxyphenyl)ethyl]-1-methyl-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(C)C(=O)C(N2CC=C(C)C)=C1N=C2N1CC(NC(=O)OC(C)(C)C)CCC1 GAFHTHIEYSJDOG-UHFFFAOYSA-N 0.000 description 1
• JORIAOLBVSWSCN-UHFFFAOYSA-N tert-butyl n-[1-[3-[2-(dimethylamino)ethyl]-7-(3-methylbut-2-enyl)-2,6-dioxo-1-(2-phenylethyl)purin-8-yl]piperidin-3-yl]carbamate Chemical compound CC(C)=CCN1C=2C(=O)N(CCC=3C=CC=CC=3)C(=O)N(CCN(C)C)C=2N=C1N1CCCC(NC(=O)OC(C)(C)C)C1 JORIAOLBVSWSCN-UHFFFAOYSA-N 0.000 description 1
• KTHRAQGWMCBMIL-UHFFFAOYSA-N tert-butyl n-[1-[3-methyl-1-[2-[3-[2-(methylamino)-2-oxoethoxy]phenyl]-2-oxoethyl]-7-(3-methylbut-2-enyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound CNC(=O)COC1=CC=CC(C(=O)CN2C(C=3N(CC=C(C)C)C(N4CC(CCC4)NC(=O)OC(C)(C)C)=NC=3N(C)C2=O)=O)=C1 KTHRAQGWMCBMIL-UHFFFAOYSA-N 0.000 description 1
• USLPPAODMRYTRS-UHFFFAOYSA-N tert-butyl n-[1-[3-methyl-7-(3-methylbut-2-enyl)-1-(1,2-oxazol-3-ylmethyl)-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CC=1C=CON=1 USLPPAODMRYTRS-UHFFFAOYSA-N 0.000 description 1
• ZOHWWZQXYPMFLA-UHFFFAOYSA-N tert-butyl n-[1-[3-methyl-7-(3-methylbut-2-enyl)-1-[(1-methylindazol-3-yl)methyl]-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4N(C)N=3)C(=O)C=2N(CC=C(C)C)C=1N1CCCC(NC(=O)OC(C)(C)C)C1 ZOHWWZQXYPMFLA-UHFFFAOYSA-N 0.000 description 1
• WKFGYQUTDJJRRQ-UHFFFAOYSA-N tert-butyl n-[1-[3-methyl-7-(3-methylbut-2-enyl)-1-[(3-methylpyridin-2-yl)methyl]-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CC1=NC=CC=C1C WKFGYQUTDJJRRQ-UHFFFAOYSA-N 0.000 description 1
• INBVKCKJKCHROH-UHFFFAOYSA-N tert-butyl n-[1-[3-methyl-7-(3-methylbut-2-enyl)-1-[(4-methylpyridin-2-yl)methyl]-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CC1=CC(C)=CC=N1 INBVKCKJKCHROH-UHFFFAOYSA-N 0.000 description 1
• DYIVXYXEUNRQKH-UHFFFAOYSA-N tert-butyl n-[1-[3-methyl-7-(3-methylbut-2-enyl)-1-[(5-methylpyridin-2-yl)methyl]-2,6-dioxopurin-8-yl]piperidin-3-yl]carbamate Chemical compound O=C1C=2N(CC=C(C)C)C(N3CC(CCC3)NC(=O)OC(C)(C)C)=NC=2N(C)C(=O)N1CC1=CC=C(C)C=N1 DYIVXYXEUNRQKH-UHFFFAOYSA-N 0.000 description 1
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